Details of the Drug

General Information of Drug (ID: DMKJ8LB)

Drug Name
Josamycin
Synonyms
Josacine; Josamicina; Josamycine; Josamycinum; EN 141; Kitasamycin A3; Leucomycin A3; Turimycin A5; Antibiotic yl-704 A3; Iosalide (TN); Josacine (TN); Josalid (TN); Josamicina [INN-Spanish]; Josamina (TN); Josamy (TN); Josamycin (TN); Josamycine [INN-French]; Josamycinum [INN-Latin]; Wilprafen (TN); Yl-704 A3; Josamycin [USAN:INN:JAN]; Josamycin (JP15/USAN/INN); Dro-2H-pyran-3-yl 3-methylbutanoate; Leucomycin V, 3-acetate 4B-(3-methylbutanoate); Leucomycin V, 3-acetate 4(sup B)-(3-methylbutanoate); Leucomycin V,3-acetate 4(sup beta)-(3-methylbutanoate)
Indication
Disease Entry ICD 11 Status REF
Bacterial infection 1A00-1C4Z Approved [1]
Therapeutic Class
Antibiotics
Drug Type
Small molecular drug
Structure
3D MOL is unavailable 2D MOL
#Ro5 Violations (Lipinski): 3 Molecular Weight (mw) 828
Logarithm of the Partition Coefficient (xlogp) 2.9
Rotatable Bond Count (rotbonds) 14
Hydrogen Bond Donor Count (hbonddonor) 3
Hydrogen Bond Acceptor Count (hbondacc) 16
Chemical Identifiers
Formula
C42H69NO15
IUPAC Name
[(2S,3S,4R,6S)-6-[(2R,3S,4R,5R,6S)-6-[[(4R,5S,6S,7R,9R,10R,11E,13E,16R)-4-acetyloxy-10-hydroxy-5-methoxy-9,16-dimethyl-2-oxo-7-(2-oxoethyl)-1-oxacyclohexadeca-11,13-dien-6-yl]oxy]-4-(dimethylamino)-5-hydroxy-2-methyloxan-3-yl]oxy-4-hydroxy-2,4-dimethyloxan-3-yl] 3-methylbutanoate
Canonical SMILES
C[C@@H]1C/C=C/C=C/[C@@H]([C@@H](C[C@@H]([C@@H]([C@H]([C@@H](CC(=O)O1)OC(=O)C)OC)O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)C)O[C@H]3C[C@@]([C@H]([C@@H](O3)C)OC(=O)CC(C)C)(C)O)N(C)C)O)CC=O)C)O
InChI
InChI=1S/C42H69NO15/c1-23(2)19-32(47)56-40-27(6)53-34(22-42(40,8)50)57-37-26(5)54-41(36(49)35(37)43(9)10)58-38-29(17-18-44)20-24(3)30(46)16-14-12-13-15-25(4)52-33(48)21-31(39(38)51-11)55-28(7)45/h12-14,16,18,23-27,29-31,34-41,46,49-50H,15,17,19-22H2,1-11H3/b13-12+,16-14+/t24-,25-,26-,27+,29+,30+,31-,34+,35-,36-,37-,38+,39+,40+,41+,42-/m1/s1
InChIKey
XJSFLOJWULLJQS-NGVXBBESSA-N
Cross-matching ID
PubChem CID
5282165
ChEBI ID
CHEBI:31739
CAS Number
16846-24-5
DrugBank ID
DB01321
TTD ID
D0X1WJ

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Bacterial 50S ribosomal RNA (Bact 50S rRNA) TTUWYEA NOUNIPROTAC Binder [2]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
ADP-ribosylation factor 1 (ARF1) OT5C4C3L ARF1_HUMAN Drug Response [3]
ATP synthase subunit beta, mitochondrial (ATP5F1B) OTLFZUQK ATPB_HUMAN Drug Response [3]
ATP synthase subunit d, mitochondrial (ATP5PD) OTAJDLE2 ATP5H_HUMAN Drug Response [3]
ATP synthase subunit O, mitochondrial (ATP5PO) OTU3MCTN ATPO_HUMAN Drug Response [3]
ATP-citrate synthase (ACLY) OTRL9ZRP ACLY_HUMAN Drug Response [3]
ATP-dependent 6-phosphofructokinase, platelet type (PFKP) OTFP7AA8 PFKAP_HUMAN Drug Response [3]
ATP-dependent Clp protease ATP-binding subunit clpX-like, mitochondrial (CLPX) OTIT4JL0 CLPX_HUMAN Drug Response [3]
ATP-dependent Clp protease proteolytic subunit, mitochondrial (CLPP) OTEPHG0S CLPP_HUMAN Drug Response [3]
Citrate synthase, mitochondrial (CS) OTYLYXMO CISY_HUMAN Drug Response [3]
Complement receptor type 1 (CR1) OTODWRW4 CR1_HUMAN Gene/Protein Processing [4]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

References

1 Drug information of Josamycin, 2008. eduDrugs.
2 The mechanism of action of macrolides, lincosamides and streptogramin B reveals the nascent peptide exit path in the ribosome. J Mol Biol. 2003 Jul 25;330(5):1005-14.
3 A genome-wide analysis of targets of macrolide antibiotics in mammalian cells. J Biol Chem. 2020 Feb 14;295(7):2057-2067. doi: 10.1074/jbc.RA119.010770. Epub 2020 Jan 8.
4 In vitro stimulation of polymorphonuclear cell adhesion by ribomunyl and antibiotic + ribomunyl combinations: effects on CD18, CD35 and CD16 expression. Int J Immunopharmacol. 1993 Feb;15(2):163-73. doi: 10.1016/0192-0561(93)90092-d.